NPASS Compound

Structure

NPC105999 OpenBabel07101719152D 25 27 0 0 0 0 0 0 0 0999 V2000 1.2330 1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6977 3.0085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4898 2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1840 1.6702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6488 3.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3920 2.6483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9272 1.0011 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.8567 4.2956 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 3.3364 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 0.3364 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3430 2.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 2.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 1 10 1 0 0 0 0 2 7 1 0 0 0 0 2 11 2 0 0 0 0 3 7 1 0 0 0 0 3 14 2 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 8 9 1 0 0 0 0 9 14 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 25 1 0 0 0 0 15 22 2 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	591.72
Volume:	365.486
LogP:	5.16
LogD:	2.337
LogS:	-4.434
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	3.105
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.907
MDCK Permeability:	1.587965016369708e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.874
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	101.74632263183594%
Volume Distribution (VD):	0.162
Pgp-substrate:	3.0621118545532227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.904
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.699
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.698
CYP2C9-substrate:	0.201
CYP2D6-inhibitor:	0.118
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.112
CYP3A4-substrate:	0.058

ADMET: Excretion

Clearance (CL):	0.086
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.676
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.808
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.897
Carcinogencity:	0.201
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.44

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC105999

Natural Product ID:	NPC105999
*Common Name:**	Rubrolide A
IUPAC Name:	(5Z)-4-(3,5-dibromo-4-hydroxyphenyl)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]furan-2-one
Synonyms:	Rubrolide A
Standard InCHIKey:	RQFYDYMMVXKTBY-BNNQUZSASA-N
Standard InCHI:	InChI=1S/C17H8Br4O4/c18-10-1-7(2-11(19)16(10)23)3-14-9(6-15(22)25-14)8-4-12(20)17(24)13(21)5-8/h1-6,23-24H/b14-3-
SMILES:	c1c(cc(c(c1Br)O)Br)/C=C1/C(=CC(=O)O1)c1cc(c(c(c1)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511842
PubChem CID:	6055630
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0002320] Halophenols [CHEMONTID:0002764] Bromophenols [CHEMONTID:0002768] O-bromophenols

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33352	pseudodistoma antinboja	Species	Pseudodistomidae	Eukaryota	n.a.	Korean	n.a.	PMID[23145884]
NPO40655	Synoicum sp. Ascidian	Strain	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31967465]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
MIC	18

Activity Type	# Activity
Individual Protein	3
Organism	18
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4717	Individual Protein	Cystathionine beta-synthase	Homo sapiens	IC50	=	108000.0	nM	PMID[558508]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	216000.0	nM	PMID[558509]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	216000.0	nM	PMID[558509]
NPT2	Others	Unspecified		IC50	=	19800.0	nM	PMID[558506]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[558507]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[558507]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1.6	ug.mL-1	PMID[558507]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	1.6	ug.mL-1	PMID[558507]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	1.6	ug.mL-1	PMID[558507]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.1	ug.mL-1	PMID[558507]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[558509]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	128.0	ug.mL-1	PMID[558509]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	128.0	ug.mL-1	PMID[558509]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	32.0	ug.mL-1	PMID[558509]
NPT25245	ORGANISM	Proteus hauseri	Proteus hauseri	MIC	=	16.0	ug.mL-1	PMID[558509]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	128.0	ug.mL-1	PMID[558509]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC105999 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	1979
0.2-0.3	6205
0.3-0.4	13474
0.4-0.5	6374
0.5-0.6	12285
0.6-0.7	1938
0.7-0.8	87
0.8-0.85	20
0.85-0.9	6
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9746	High Similarity	NPC213414
0.9576	High Similarity	NPC296202
0.9492	High Similarity	NPC7830
0.935	High Similarity	NPC478071
0.9274	High Similarity	NPC11449
0.9032	High Similarity	NPC159987
0.9032	High Similarity	NPC122359
0.9032	High Similarity	NPC78061
0.8855	High Similarity	NPC81137
0.8657	High Similarity	NPC147137
0.8547	High Similarity	NPC54543
0.8529	High Similarity	NPC270848
0.8529	High Similarity	NPC272868
0.8529	High Similarity	NPC122599
0.8421	Intermediate Similarity	NPC177967
0.8421	Intermediate Similarity	NPC471237
0.839	Intermediate Similarity	NPC79543
0.8319	Intermediate Similarity	NPC473358
0.824	Intermediate Similarity	NPC180207
0.8222	Intermediate Similarity	NPC197766
0.8222	Intermediate Similarity	NPC471236
0.8169	Intermediate Similarity	NPC471235
0.8169	Intermediate Similarity	NPC470710
0.8169	Intermediate Similarity	NPC235033
0.8169	Intermediate Similarity	NPC73132
0.8151	Intermediate Similarity	NPC471495
0.8047	Intermediate Similarity	NPC116562
0.7984	Intermediate Similarity	NPC296526
0.7967	Intermediate Similarity	NPC471488
0.7891	Intermediate Similarity	NPC471486
0.7869	Intermediate Similarity	NPC183700
0.7823	Intermediate Similarity	NPC33244
0.7795	Intermediate Similarity	NPC311091
0.7795	Intermediate Similarity	NPC471033
0.7778	Intermediate Similarity	NPC128249
0.7705	Intermediate Similarity	NPC206341
0.7664	Intermediate Similarity	NPC471328
0.7623	Intermediate Similarity	NPC260952
0.7619	Intermediate Similarity	NPC94217
0.7603	Intermediate Similarity	NPC127676
0.7597	Intermediate Similarity	NPC38483
0.7518	Intermediate Similarity	NPC259017
0.746	Intermediate Similarity	NPC17693
0.744	Intermediate Similarity	NPC471487
0.7372	Intermediate Similarity	NPC99280
0.736	Intermediate Similarity	NPC473372
0.7353	Intermediate Similarity	NPC13004
0.7344	Intermediate Similarity	NPC115803
0.7333	Intermediate Similarity	NPC220311
0.7328	Intermediate Similarity	NPC141791
0.7328	Intermediate Similarity	NPC100395
0.7328	Intermediate Similarity	NPC263386
0.7319	Intermediate Similarity	NPC475735
0.7313	Intermediate Similarity	NPC212541
0.7313	Intermediate Similarity	NPC14141
0.7302	Intermediate Similarity	NPC63345
0.7295	Intermediate Similarity	NPC304638
0.7273	Intermediate Similarity	NPC253746
0.7259	Intermediate Similarity	NPC288945
0.7259	Intermediate Similarity	NPC236265
0.7254	Intermediate Similarity	NPC213471
0.7252	Intermediate Similarity	NPC275519
0.7234	Intermediate Similarity	NPC245386
0.7218	Intermediate Similarity	NPC470849
0.7218	Intermediate Similarity	NPC470848
0.7203	Intermediate Similarity	NPC271942
0.7197	Intermediate Similarity	NPC117759
0.7197	Intermediate Similarity	NPC264976
0.719	Intermediate Similarity	NPC171843
0.719	Intermediate Similarity	NPC130193
0.7188	Intermediate Similarity	NPC131530
0.7174	Intermediate Similarity	NPC219923
0.7164	Intermediate Similarity	NPC147654
0.7154	Intermediate Similarity	NPC51345
0.7154	Intermediate Similarity	NPC135784
0.7143	Intermediate Similarity	NPC32977
0.7143	Intermediate Similarity	NPC81010
0.7143	Intermediate Similarity	NPC474753
0.7122	Intermediate Similarity	NPC474091
0.712	Intermediate Similarity	NPC70843
0.7109	Intermediate Similarity	NPC139946
0.7107	Intermediate Similarity	NPC201967
0.7103	Intermediate Similarity	NPC474128
0.7087	Intermediate Similarity	NPC75272
0.7087	Intermediate Similarity	NPC471954
0.7083	Intermediate Similarity	NPC156356
0.7071	Intermediate Similarity	NPC473724
0.7063	Intermediate Similarity	NPC309667
0.7063	Intermediate Similarity	NPC156648
0.7059	Intermediate Similarity	NPC84606
0.7059	Intermediate Similarity	NPC474169
0.7059	Intermediate Similarity	NPC473572
0.7055	Intermediate Similarity	NPC89341
0.705	Intermediate Similarity	NPC79332
0.705	Intermediate Similarity	NPC217431
0.7045	Intermediate Similarity	NPC122117
0.7042	Intermediate Similarity	NPC303993
0.704	Intermediate Similarity	NPC243677
0.7029	Intermediate Similarity	NPC213552
0.7029	Intermediate Similarity	NPC120225
0.7016	Intermediate Similarity	NPC68269
0.7016	Intermediate Similarity	NPC91820
0.7016	Intermediate Similarity	NPC82426
0.7016	Intermediate Similarity	NPC470202
0.7007	Intermediate Similarity	NPC184632
0.7007	Intermediate Similarity	NPC135349
0.7	Intermediate Similarity	NPC474614
0.7	Intermediate Similarity	NPC151715
0.7	Intermediate Similarity	NPC59387
0.6992	Remote Similarity	NPC309434
0.6992	Remote Similarity	NPC203124
0.6985	Remote Similarity	NPC229213
0.6985	Remote Similarity	NPC219444
0.6984	Remote Similarity	NPC95178
0.6984	Remote Similarity	NPC92623
0.6984	Remote Similarity	NPC29989
0.6984	Remote Similarity	NPC135464
0.6984	Remote Similarity	NPC113457
0.6984	Remote Similarity	NPC69332
0.698	Remote Similarity	NPC71629
0.6978	Remote Similarity	NPC473708
0.6978	Remote Similarity	NPC474147
0.6975	Remote Similarity	NPC45040
0.6972	Remote Similarity	NPC303011
0.697	Remote Similarity	NPC19290
0.6968	Remote Similarity	NPC474535
0.696	Remote Similarity	NPC109637
0.696	Remote Similarity	NPC2518
0.6957	Remote Similarity	NPC289459
0.6957	Remote Similarity	NPC142776
0.6957	Remote Similarity	NPC168259
0.6953	Remote Similarity	NPC88141
0.695	Remote Similarity	NPC30390
0.6942	Remote Similarity	NPC246679
0.6942	Remote Similarity	NPC26244
0.6935	Remote Similarity	NPC94343
0.6934	Remote Similarity	NPC285345
0.6934	Remote Similarity	NPC306100
0.6934	Remote Similarity	NPC473942
0.6929	Remote Similarity	NPC2596
0.6923	Remote Similarity	NPC71888
0.6923	Remote Similarity	NPC120114
0.6923	Remote Similarity	NPC475697
0.6918	Remote Similarity	NPC160932
0.6917	Remote Similarity	NPC183154
0.6917	Remote Similarity	NPC610
0.6917	Remote Similarity	NPC175799
0.6917	Remote Similarity	NPC278652
0.6917	Remote Similarity	NPC200988
0.6917	Remote Similarity	NPC65791
0.6917	Remote Similarity	NPC263754
0.6917	Remote Similarity	NPC145023
0.6912	Remote Similarity	NPC136543
0.6912	Remote Similarity	NPC187868
0.6911	Remote Similarity	NPC245561
0.6906	Remote Similarity	NPC43706
0.6905	Remote Similarity	NPC233396
0.6905	Remote Similarity	NPC303141
0.6905	Remote Similarity	NPC154899
0.6899	Remote Similarity	NPC21162
0.6897	Remote Similarity	NPC474673
0.6892	Remote Similarity	NPC78530
0.6892	Remote Similarity	NPC470472
0.6885	Remote Similarity	NPC473388
0.6884	Remote Similarity	NPC10154
0.6884	Remote Similarity	NPC474532
0.6884	Remote Similarity	NPC246704
0.6884	Remote Similarity	NPC89630
0.6884	Remote Similarity	NPC265413
0.6879	Remote Similarity	NPC83062
0.6879	Remote Similarity	NPC477300
0.6879	Remote Similarity	NPC214246
0.6875	Remote Similarity	NPC281604
0.6875	Remote Similarity	NPC470039
0.6875	Remote Similarity	NPC31274
0.687	Remote Similarity	NPC95381
0.687	Remote Similarity	NPC76400
0.6867	Remote Similarity	NPC296085
0.6866	Remote Similarity	NPC86198
0.686	Remote Similarity	NPC128062
0.6857	Remote Similarity	NPC288416
0.6855	Remote Similarity	NPC52472
0.6853	Remote Similarity	NPC76453
0.6853	Remote Similarity	NPC300678
0.6853	Remote Similarity	NPC243404
0.6853	Remote Similarity	NPC173034
0.685	Remote Similarity	NPC188677
0.6846	Remote Similarity	NPC297657
0.6846	Remote Similarity	NPC470355
0.6846	Remote Similarity	NPC226250
0.6842	Remote Similarity	NPC281277
0.6842	Remote Similarity	NPC258222
0.6838	Remote Similarity	NPC252149
0.6835	Remote Similarity	NPC137416
0.6835	Remote Similarity	NPC197832
0.6835	Remote Similarity	NPC88403
0.6835	Remote Similarity	NPC67951
0.6831	Remote Similarity	NPC226493
0.6831	Remote Similarity	NPC160081
0.6831	Remote Similarity	NPC32463

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC105999 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	1100
0.2-0.3	1640
0.3-0.4	3214
0.4-0.5	1845
0.5-0.6	972
0.6-0.7	101
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7372	Intermediate Similarity	NPD9718	Approved
0.719	Intermediate Similarity	NPD2296	Approved
0.7078	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD2934	Approved
0.7	Intermediate Similarity	NPD2933	Approved
0.6942	Remote Similarity	NPD2859	Approved
0.6942	Remote Similarity	NPD2860	Approved
0.6923	Remote Similarity	NPD5535	Approved
0.6912	Remote Similarity	NPD1535	Discovery
0.6866	Remote Similarity	NPD1894	Discontinued
0.6861	Remote Similarity	NPD1481	Phase 2
0.6831	Remote Similarity	NPD3764	Approved
0.6825	Remote Similarity	NPD9244	Approved
0.6805	Remote Similarity	NPD4287	Approved
0.6788	Remote Similarity	NPD422	Phase 1
0.6774	Remote Similarity	NPD3020	Approved
0.6719	Remote Similarity	NPD3134	Approved
0.6715	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD1358	Approved
0.6643	Remote Similarity	NPD3225	Approved
0.6618	Remote Similarity	NPD9545	Approved
0.6596	Remote Similarity	NPD2797	Approved
0.6596	Remote Similarity	NPD1203	Approved
0.6589	Remote Similarity	NPD968	Approved
0.6522	Remote Similarity	NPD4626	Approved
0.6512	Remote Similarity	NPD9697	Approved
0.6507	Remote Similarity	NPD4060	Phase 1
0.6483	Remote Similarity	NPD3268	Approved
0.6475	Remote Similarity	NPD3496	Discontinued
0.6463	Remote Similarity	NPD4340	Discontinued
0.6454	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1169	Approved
0.6439	Remote Similarity	NPD3021	Approved
0.6439	Remote Similarity	NPD3022	Approved
0.6434	Remote Similarity	NPD5909	Discontinued
0.6414	Remote Similarity	NPD7095	Approved
0.6412	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2935	Discontinued
0.6387	Remote Similarity	NPD111	Approved
0.6377	Remote Similarity	NPD1548	Phase 1
0.637	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.637	Remote Similarity	NPD2313	Discontinued
0.637	Remote Similarity	NPD6798	Discontinued
0.6358	Remote Similarity	NPD7266	Discontinued
0.6351	Remote Similarity	NPD6355	Discontinued
0.635	Remote Similarity	NPD9493	Approved
0.635	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD2614	Approved
0.6343	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.634	Remote Similarity	NPD3750	Approved
0.6333	Remote Similarity	NPD2799	Discontinued
0.6331	Remote Similarity	NPD5691	Approved
0.6328	Remote Similarity	NPD1242	Phase 1
0.6328	Remote Similarity	NPD3028	Approved
0.6327	Remote Similarity	NPD6233	Phase 2
0.6327	Remote Similarity	NPD4062	Phase 3
0.6324	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.632	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD5163	Phase 2
0.6294	Remote Similarity	NPD1283	Approved
0.6276	Remote Similarity	NPD5736	Approved
0.6275	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.627	Remote Similarity	NPD1809	Phase 2
0.6268	Remote Similarity	NPD1608	Approved
0.6268	Remote Similarity	NPD9717	Approved
0.6257	Remote Similarity	NPD2802	Phase 3
0.625	Remote Similarity	NPD3267	Approved
0.625	Remote Similarity	NPD1164	Approved
0.625	Remote Similarity	NPD1241	Discontinued
0.625	Remote Similarity	NPD3266	Approved
0.6241	Remote Similarity	NPD2684	Approved
0.6234	Remote Similarity	NPD4628	Phase 3
0.6225	Remote Similarity	NPD4308	Phase 3
0.6224	Remote Similarity	NPD6583	Phase 3
0.6224	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6582	Phase 2
0.6222	Remote Similarity	NPD228	Approved
0.6222	Remote Similarity	NPD969	Suspended
0.6197	Remote Similarity	NPD1610	Phase 2
0.6194	Remote Similarity	NPD5451	Approved
0.619	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD5536	Phase 2
0.6184	Remote Similarity	NPD1519	Approved
0.6184	Remote Similarity	NPD1537	Approved
0.6184	Remote Similarity	NPD1538	Phase 1
0.6184	Remote Similarity	NPD1523	Approved
0.6184	Remote Similarity	NPD1522	Approved
0.6176	Remote Similarity	NPD7843	Approved
0.6174	Remote Similarity	NPD4140	Approved
0.6164	Remote Similarity	NPD2861	Phase 2
0.6159	Remote Similarity	NPD6671	Approved
0.6159	Remote Similarity	NPD255	Approved
0.6159	Remote Similarity	NPD256	Approved
0.6154	Remote Similarity	NPD846	Approved
0.6154	Remote Similarity	NPD7440	Discontinued
0.6154	Remote Similarity	NPD940	Approved
0.6144	Remote Similarity	NPD2344	Approved
0.6133	Remote Similarity	NPD5124	Phase 1
0.6133	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD5283	Phase 1
0.6129	Remote Similarity	NPD8166	Discontinued
0.6124	Remote Similarity	NPD1238	Approved
0.6122	Remote Similarity	NPD6832	Phase 2
0.6122	Remote Similarity	NPD4908	Phase 1
0.6119	Remote Similarity	NPD74	Approved
0.6119	Remote Similarity	NPD9266	Approved
0.6118	Remote Similarity	NPD7033	Discontinued
0.6115	Remote Similarity	NPD9568	Approved
0.6111	Remote Similarity	NPD845	Approved
0.6107	Remote Similarity	NPD4870	Approved
0.6107	Remote Similarity	NPD6663	Approved
0.6104	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD5585	Approved
0.6096	Remote Similarity	NPD6584	Phase 3
0.609	Remote Similarity	NPD2354	Approved
0.609	Remote Similarity	NPD6190	Approved
0.6084	Remote Similarity	NPD1611	Approved
0.6084	Remote Similarity	NPD1281	Approved
0.6078	Remote Similarity	NPD1551	Phase 2
0.6074	Remote Similarity	NPD2067	Discontinued
0.6069	Remote Similarity	NPD1876	Approved
0.6067	Remote Similarity	NPD1240	Approved
0.6065	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD2497	Approved
0.6058	Remote Similarity	NPD2496	Approved
0.6058	Remote Similarity	NPD821	Approved
0.6056	Remote Similarity	NPD17	Approved
0.6056	Remote Similarity	NPD5846	Approved
0.6056	Remote Similarity	NPD3019	Approved
0.6056	Remote Similarity	NPD2932	Approved
0.6056	Remote Similarity	NPD6516	Phase 2
0.6054	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD1520	Approved
0.6053	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD1521	Approved
0.6053	Remote Similarity	NPD7097	Phase 1
0.6053	Remote Similarity	NPD1536	Approved
0.6048	Remote Similarity	NPD689	Discontinued
0.6045	Remote Similarity	NPD9264	Approved
0.6045	Remote Similarity	NPD2342	Discontinued
0.6045	Remote Similarity	NPD9267	Approved
0.6045	Remote Similarity	NPD9263	Approved
0.6043	Remote Similarity	NPD7157	Approved
0.6043	Remote Similarity	NPD4198	Discontinued
0.6042	Remote Similarity	NPD3972	Approved
0.604	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD2346	Discontinued
0.6039	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD987	Approved
0.6026	Remote Similarity	NPD230	Phase 1
0.6026	Remote Similarity	NPD7003	Approved
0.6016	Remote Similarity	NPD1282	Approved
0.6016	Remote Similarity	NPD844	Approved
0.6014	Remote Similarity	NPD2228	Approved
0.6014	Remote Similarity	NPD2234	Approved
0.6014	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD2229	Approved
0.6013	Remote Similarity	NPD3748	Approved
0.6013	Remote Similarity	NPD1510	Phase 2
0.6	Remote Similarity	NPD5958	Discontinued
0.6	Remote Similarity	NPD1549	Phase 2
0.6	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD2309	Approved
0.5987	Remote Similarity	NPD1607	Approved
0.5986	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD2798	Approved
0.5985	Remote Similarity	NPD6647	Phase 2
0.5985	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD1202	Approved
0.5975	Remote Similarity	NPD3536	Discontinued
0.5974	Remote Similarity	NPD4476	Approved
0.5974	Remote Similarity	NPD5404	Approved
0.5974	Remote Similarity	NPD5406	Approved
0.5974	Remote Similarity	NPD5405	Approved
0.5974	Remote Similarity	NPD5408	Approved
0.5974	Remote Similarity	NPD4477	Approved
0.5973	Remote Similarity	NPD3027	Phase 3
0.5969	Remote Similarity	NPD288	Approved
0.596	Remote Similarity	NPD4307	Phase 2
0.596	Remote Similarity	NPD2979	Phase 3
0.5959	Remote Similarity	NPD196	Phase 1
0.5954	Remote Similarity	NPD289	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD454	Approved
0.5944	Remote Similarity	NPD1778	Approved
0.5944	Remote Similarity	NPD2667	Approved
0.5944	Remote Similarity	NPD2668	Approved
0.5942	Remote Similarity	NPD7635	Approved
0.594	Remote Similarity	NPD9608	Approved
0.594	Remote Similarity	NPD9610	Approved
0.5938	Remote Similarity	NPD5049	Phase 3
0.5938	Remote Similarity	NPD6273	Approved
0.5935	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD2353	Approved
0.5933	Remote Similarity	NPD1296	Phase 2
0.5933	Remote Similarity	NPD3374	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data